Villas with a pool Montepulciano | Apartments to rent with swimming facilities | Holiday Lettings

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150 Holiday homes

Filters applied: Swimming pool (150)

(11) Excellent 

21

charming cottage in peaceful country setting - Gracciano cottage sleeps 6

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
The cottage is opposite the owner's house and consists of two double bedrooms, two bathrooms and a large living room with cooking area. The living area opens onto a patio and pergola and the downstairs bedroom also opens onto a small patio. There is access for the disa  …see more

from £70 / night

£383 - £1792 / week

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from £70 / night

21

Lovely room in farmhouse in Montepulciano - Acquaviva di Montepulciano b&b sleeps 2

Montepulciano / Acquaviva di Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Tenuta di Argiano a Montepulciano, located near MONTEPULCIANO, is surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulciano, and is peaceful and quite. swimming pool and wifi . La Giara (35 m2) studio  …see more

from £60 / night

£414 / week

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from £60 / night

(7) Excellent 

33

Lovely 2 bedroom holiday apartment in Tuscany - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
The apartment Tino is 55 Square meters and accommodates up to 4 people. First floor is composed of sitting/dining room with cooking area (dishwasher) and fireplace, 2 bedrooms, 1 bathroom with shower. sofabed for one people in living room for a child. In the garden ,  …see more

from £61 / night

£461 - £592 / week

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from £61 / night

17

Holiday Resort in Montepulciano M - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £48 / night

£335 - £700 / week

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from £48 / night

(8) Excellent 

41

Unique, charming farmhouse in Tuscany countryside with shared outdoor pool, sleeps up to 6 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
The main arched entrance leads past a utility room and downstairs bathroom into the open plan kitchen and dining room with dining table for 6 guests. The lounge has two sofa's one of which is a comfortable double sofa bed There is a wood burning stove in the lounge  …see more

from £72 / night

£500 - £775 / week

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from £72 / night

18

The Artist's Villa (v042) - Gracciano villa sleeps 9

Montepulciano / Gracciano

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This unique villa has, on the ground floor, a large entrance hall, a large living room with kitchen, dining room and central fireplace, a double bedroom, a bedroom with french bed (which could sleep 2 people), a bathroom with a shower, a bathroom with bathtub. On the fi  …see more

from £210 / night

£1470 - £1766 / week

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from £210 / night

(4) Very Good 

24

Great place for a Tuscan family holiday, 2 bedroom countryside apartments with shared pool - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Tenuta di Argiano a Montepulciano Please ask always AVAILABILITY , we will find in one of our structures the ideal place for your holiday. CAR IS NECESSARY WE ARE IN THE MIDDLE OF COUNTRYSIDE, SURROUNDED BY NATURE. The beautiful apartment FIASCO (60square Mt) , FOR  …see more

from £61 / night

£427 / week

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from £61 / night

40

Il Molinaccio di Montepulciano 1 - Montepulciano farmhouse sleeps 2

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
The watermill “Il Molinaccio”, near the renaissance town of Montepulciano, was already present in the old maps of the Granduchy of Tuscany . The original building, duly and let me say passionately restored, now reopens as a luxury country house where the guests may  …see more

from £96 / night

£522 / week

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from £96 / night

(2) Excellent 

17

Holiday Resort in Montepulciano T - Montepulciano apartment sleeps 5

Province of Siena / Montepulciano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearestt village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £74 / night

£496 - £1005 / week

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from £74 / night

24

Villa in Tuscany - Montepulciano villa sleeps 12

Province of Siena / Montepulciano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The Poggio Golo holiday villa has been restored to its original splendour after long and careful renovation, giving you the possibility to savor the atmosphere of a holiday from past times in an old 17th century villa with original furniture and accessories. The well-tr  …see more

from £218 / night

£2131 / week

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from £218 / night

(1) Excellent 

20

Holiday Resort in Montepuciano B - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £60 / night

£418 - £822 / week

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from £60 / night

(3) Very Good 

24

Pietra del Diavolo - Montepulciano farmhouse sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
Villa Pietra del Diavolo, recently restored, is situated in one of the most beautiful and panoramic hill around Montepulciano.“Pietra del Diavolo” is named after a stone composed of tufa layers particularly common in the local area.The property is situated in the he  …see more

from £237 / night

£1653 - £2000 / week

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from £237 / night

(1) Excellent 

23

Tuscan Villa Argiano 1 room ,Montepulciano, B&B - Montepulciano villa sleeps 2

Province of Siena / Montepulciano

4 2 2 nights min

  • 4 bedrooms
  • Sleeps 2
  • 2 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Ask owner if suitable for children
in Villa Argiano in Montepulciano, we have several possibilities : B&B in Argiano's villa rooms ( three ) or self catering apartments ( two + one extra room ) in farmhouse fattoriadiargiano dot it. In this beautiful Villa, were we live , at the second floor of th  …see more

from £61 / night

£427 / week

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from £61 / night

100

Petit Verdot - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
ExteriorsOriginally built in the 17th century rural Tuscany, the Villa has been restored without altering its original architecture. Siena's typical ocher colors dominate the villa's stone walls and diffuse a welcoming glow on the light blue of the infinity pool. All ar  …see more

from £435 / night

£3044 - £3392 / week

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from £435 / night

26

Villa Croce - Sant'Albino villa sleeps 10

Montepulciano / Sant'Albino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano. The property is situated in the heart a working farm with breathtaking views over the valley where Vino Nobile di Montepulciano is produced. The villa ha  …see more

from £237 / night

£1653 - £3131 / week

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from £237 / night

100

Vino Nobile - Giardino - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Located amidst the enchanting garden of the property, this independent cottage in Montepulciano affords a dining area and a living room with fireplace and double sofa bed, a kitchen with its own breakfast area, and a double bedroom with its en-suite bathroom equipped wi  …see more

from £105 / night

£653 - £853 / week

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from £105 / night

100

Vino Nobile - Vigna - Montepulciano apartment sleeps 3

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
This charming cottage in Montepulciano affords a dining area and a living room with fireplace and single sofa bed, a kitchenette and a double/twin bedroom. The cottage also has its own private bathroom with shower.Outside, it features its own private terrace. The cottag  …see more

from £105 / night

£609 - £809 / week

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from £105 / night

(1) Excellent 

7

Il Casalone Apartment Oliveto - Montepulciano farmhouse sleeps 4

Province of Siena / Montepulciano

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Located in a panoramic position on a hill crest between the Val d'Orcia and Valdichiana near Montepulciano, Agriturismo Il Casalone offers a holiday unit tastefully furnished in Tuscan country style. One double bed room (king size), one bathroom and a living room w  …see more

from £53 / night

£235 - £453 / week

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from £53 / night

7

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £66 / night

£383 - £609 / week

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from £66 / night

100

Vino Nobile - Fontana - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
This enchanting suite in Montepulciano affords a dining-com-living area and a kitchen corner. The bedroom has a comfortable double bed and it affords an en-suite bathroom with whirlpool shower. The design of this suite is very peculiar, since the furniture has been crea  …see more

from £87 / night

£609 - £740 / week

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from £87 / night

30

Beautiful Tuscany Villa , swimming pool, wifi - Montepulciano watermill sleeps 6

Province of Siena / Montepulciano

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 16 km
  • Swimming pool
  • Child friendly
Beutiful old structure located in one of the most unspoiled place in Tuscany. Peace and relax. Private garden with swimming pool , wifi, and inside parking. Villa for 6 people and another annex , for 4 people , is ideal for family or friends groups for a total of 10 p  …see more

from £148 / night

£974 - £1522 / week

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from £148 / night

6

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £61 / night

£366 - £496 / week

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from £61 / night

24

La Poliziana - 6 pax + kitchen - Montepulciano apartment sleeps 8

Province of Siena / Montepulciano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
This apartment in Montepulciano hosting a maximum of 8 guests is approximately 95 sq-m and affords views of the surrounding beauty.The apartment  features a kitchen corner to try your hand at Tuscan cuisine and a lovely 3 double bedroom and 1 twin bedroom bedecked  …see more

from £286 / night

£2000 - £2609 / week

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from £286 / night

83

il Molinaccio Montepulciano 3 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
The watermill “Il Molinaccio”, near the renaissance town of Montepulciano, was already present in the old maps of the Granduchy of Tuscany . The original building, duly and let me say passionately restored, now reopens as a luxury country house where the guests may  …see more

from £261 / night

£1522 / week

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from £261 / night

21

Villa Bacco with Pool (Max 16+4 ppl) - Valiano villa sleeps 20

Montepulciano / Valiano

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
Villa located on top of a hill and dipped between wineyards.Due to its strategic position, in Valiano di Montepulciano, half way from Rome to Florence and on the border between Tuscany and Umbria region, it will be easy to visit the most artistic towns in the heart of I  …see more

from £621 / night

£3914 / week

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from £621 / night

5

Montepulciano / Valiano

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £114 / night

£661 / week

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from £114 / night

23

I Tigli - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
I Tigli is a splendid apartment with two bedrooms and two bathrooms which is part of a property with a total of 6 apartments sharing a pool. Located in the magnificent atmosphere of the hills surrounding the ancient town of Montepulciano, famous for its history, art, ar  …see more

from £100 / night

£653 - £861 / week

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from £100 / night

100

Nobile - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
ExteriorVilla Nobile, a lovely farmhouse within a wine and olive oil producing estate boasts a perfect location, on a hill with panoramic views of the area, conveniently situated a few minutes drive from Montepulciano and well located to explore the wider area. Guests a  …see more

from £237 / night

£1653 - £2000 / week

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from £237 / night

34

Podere Sant' Albino - Sant'Albino villa sleeps 14

Montepulciano / Sant'Albino

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves. It has been turned into a residence of refined charm that retains an atmosphere of informal welcome. The landscape and environment of Montepulciano are amo  …see more

from £373 / night

£2609 - £5392 / week

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from £373 / night

5

ARDENEX2 - Montepulciano farmhouse sleeps 2

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Ardene is located in Montepulciano and due to its unexpected, innovative and welcoming accommodation facilities it is one of the most exclusive farmhouse of this area. It is a country house in ancient stone and its origins date back to the medieval times. Ardene is the  …see more

from £105 / night

£731 / week

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from £105 / night

(1) Excellent 

100

Albino - Montepulciano villa sleeps 14

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
ExteriorVilla Albino is a sophisticated and at the same time relaxed villa for 14 people in Tuscany. It is conveniently located just 5km away from Montepulciano, a privileged position to explore all of central Italy. It is within easy reach of Pienza, Montalcino, Bagno,  …see more

from £348 / night

£2435 - £5392 / week

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from £348 / night

(5) Excellent 

16

PODERE SAN PIETRO - Montepulciano farmhouse sleeps 10

Province of Siena / Montepulciano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Podere san Pietro is an ancient country house held in brick and stones with a living surface of 350 sqm. for a total of 3bathroom and 4 bedrooms, which accommodate up to 10 people , in addition to private swimming pool of 11X5 mt The house has been recently restored (20  …see more

from £174 / night

£1218 - £1557 / week

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from £174 / night

10

Agriturismo Terrarossa 2 pax - Valiano apartment sleeps 2

Montepulciano / Valiano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
The apartment "Rosa" (2 persons), with furniture of epoch, is composed of a stay- kitchen with read couch, a double bedroom and a bathroom with shower. In bedroom: tv sat. The Terrarossa agriturism complex is situated on one of the most beautiful and panoramic  …see more

from £83 / night

£392 - £479 / week

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from £83 / night

15

35827-Apartment Montepulciano - Abbadia di Montepulciano apartment sleeps 4

Montepulciano / Abbadia di Montepulciano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Elegant house restored in the second half of the 1800s. It is situated in a property of approximately 12 hectares where there are olive trees and a vineyard from which an excellent Chianti wine (D.O.C.G.) and the famous Nobile di Montepulciano (D.O.C.G.) wine are made.  …see more

from £93 / night

£645 / week

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from £93 / night

100

Foiano Della Chiana 15663 - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
Beautiful 5-hectare estate in Tuscany, a villa for wedding celebration and holidays, comprising a farmhouse of 140 m2 and an outbuilding of 60 m2 which have been skilfully restored and turned into a delightful independent villa offering tastefully and refined furnished  …see more

from £160 / night

£1119 - £2203 / week

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from £160 / night

100

Cortona 15664 - Montepulciano villa sleeps 13

Province of Siena / Montepulciano

5 13 7 nights min

  • 5 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
Charming share of an independent Tuscan villa rental affording extensive views over the surrounding landscape. The villa rental, offering tastefully furnished interiors, is quietly situated in a short distance from the lovely Tuscan town of Cortona (15 km). Distances: f  …see more

from £144 / night

£1007 - £2240 / week

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from £144 / night

29

Province of Siena / Montepulciano

5 9 1 night min

  • 5 bedrooms
  • Sleeps 9
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden

 …see more

from £870 / night

£6087 / week

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from £870 / night

55

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £70 / night

£740 - £827 / week

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from £70 / night

14

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £66 / night

£435 - £514 / week

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from £66 / night

(15) Very Good 

97

7 bedroom Tuscan farmhouse near rennaissance town of Montepulciano, features include jacuzzi, private garden and pool - Montepulciano farmhouse sleeps 16

Province of Siena / Montepulciano

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
The watermill “Il Molinaccio”, near the renaissance town of Montepulciano, was already present in the old maps of the Granduchy of Tuscany . The original building, duly and let me say passionately restored, now reopens as a luxury country house where the guests may  …see more

from £522 / night

£3044 / week

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from £522 / night

Top Destination reviews

La Casina Toscana, central with parking and wi-fi
Clean, comfortable and cozy house with privacy and convenience to Montepuciano

We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close enough to walk to the Montepulciano town. The place was very clean and thoughtf … see more
Luxury 4 bed house with views over Montepulciano
Amazing Location and Hospitality

We enjoyed a very relaxing week at La Casina with two other couples in July 2016. The villa is very spacious, well appointed and comfortable, and the kitchen is well equipped. La Casina has a commanding view of the surrounding vineyards and olive g … see more
The Beautiful Sun Apartment
Well maintained apartment and very helpful owner

Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and everything we needed was there. All to a good s … see more

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